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2'（β）-羟乙基和4'（α）-羟甲基卡波定类似物的合成及其抗丙型肝炎病毒活性

Synthesis and anti-hepatitis C virus activity of 2'(beta)-hydroxyethyl and 4'(alpha)-hydroxymethyl carbodine analogues.

作者信息

Liu Lian Jin, Hong Joon Hee

机构信息

BK21-Project Team, College of Pharmacy, Chosun University, Kwangju, Republic of Korea.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2009 Nov;28(11):1007-15. doi: 10.1080/15257770903362248.

DOI:10.1080/15257770903362248
PMID:20183569
Abstract

2'(beta)-Hydroxyethylated adenosine is a potent and selective inhibitor of hepatitis C virus (HCV) replication targeting the RNA-dependent RNA polymerase of HCV, NS5B. The synthesis and anti-HCV evaluation of carbodine analogues are described. The cyclopentene intermediate 10 was successfully made via sequential Johnson-Claisen orthoester rearrangement and ring-closing metathesis. Coupling of bases via a Pd(0) catalyst, selective dihydroxylation, and desilylation yielded the target carbodine analogues. Cytosine analogue 17 weakly inhibited the replication of the HCV replicon in Hua-7 cells by 50% at 21.1 muM.

摘要

2'（β）-羟乙基化腺苷是一种针对丙型肝炎病毒（HCV）的RNA依赖性RNA聚合酶NS5B的强效且选择性的HCV复制抑制剂。本文描述了卡波定类似物的合成及抗HCV评估。通过连续的约翰逊-克莱森原酸酯重排和闭环复分解成功制备了环戊烯中间体10。通过钯（0）催化剂进行碱基偶联、选择性双羟基化和脱硅反应，得到了目标卡波定类似物。胞嘧啶类似物17在21.1 μM时对Hua-7细胞中HCV复制子的复制有微弱抑制作用，抑制率为50%。

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